Claims
- 1. A compound of the formula (II): ##STR116## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a pharmaceutically acceptable ester group; A.sub.1 is hydrogen; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is hydrogen or hydroxyl; R.sub.3 is hydrogen or lower alkyl; and R.sub.4 is CHX wherein X is oxygen or CR.sub.6 R.sub.7 wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lower alkyl or R.sub.7 is joined to R.sub.6 to form part of a carbocyclic ring of 5 to 7 carbon atoms or R.sub.4 is CH.dbd.CHCO.sub.2 R.sub.9, CH.dbd.CHCOR.sub.9 or CH.dbd.CHR.sub.10 wherein R.sub.9 is methyl, ethyl or benzyl and R.sub.10 is hydrogen, methyl, ethyl or benzyl.
- 2. A compound according to claim 1 wherein R.sub.4 is CHO, CH.dbd.CHCO.sub.2 R.sub.9, CH.dbd.CHCOR.sub.9 or CH.dbd.CHR.sub.10 wherein R.sub.9 is methyl, ethyl or benzyl and R.sub.10 is hydrogen, methyl, ethyl or benzyl.
- 3. A compound according to claim 1 wherein R.sub.3 is hydrogen or methyl.
- 4. A compound according to claim 1 which has the cis-configuration about the .beta.-lactam ring.
- 5. A compound according to claim 1 which has the trans-configuration about the .beta.-lactam ring.
- 6. A compound according to claim 1 wherein R.sub.1 is alkyl of up to 12 carbon atoms, alkenyl groups of up to 8 carbon atoms, phenyl or benzyl or said alkyl, alkenyl, phenyl or benzyl substituted by lower alkoxyl, lower acyloxyl, halogen or nitro.
- 7. A compound according to claim 1 wherein R.sub.1 is lower alkyl unsubstituted or substituted by lower alkoxyl.
- 8. A compound according to claim 1 wherein R.sub.1 is benzyl unsubstituted or substituted by lower alkoxyl, nitro or chlorine.
- 9. A compound according to claim 1 wherein R.sub.1 is a group of the sub-formula (a) or (b): ##STR117## wherein A.sub.3 is hydrogen or methyl; A.sub.4 is lower alkyl, lower alkoxyl, phenyl, phenoxyl, benzyl or benzyloxyl; A.sub.5 is hydrogen, methyl or methoxyl; and A.sub.6 is hydrogen, methyl or methoxyl, or R.sub.1 is phthalidyl or phthalimidomethyl.
- 10. A compound according to claim 1 wherein R.sub.1 is benzyl.
- 11. A compound according to claim 1 wherein R.sub.1 is p-nitrobenzyl.
- 12. A compound according to claim 1 wherein R.sub.1 is phthalidyl.
- 13. A compound according to claim 1 which is benzyl 6-(2-oxoethyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 14. A compound according to claim 1 which is benzyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 15. The compound which is 2,2,2-trichloroethyl-6-(3-methoxycarbonyl2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 16. A compound according to claim 1 which is phthalidyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 17. A compound according to claim 1 which is phthalimidomethyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 18. A compound according to claim 1 which is phthalidyl 6-(2-oxoethyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 19. A compound according to claim 1 which is phthalidyl 6-(4-oxo-2-penten-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 20. A compound according to claim 1 which is pivaloyloxymethyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 21. A compound according to claim 1 which is p-nitrobenzyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 22. A compound according to claim 1 which is benzyl 6-(3-cyano-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 23. A compound according to claim 1 which is benzyl 6-(4-oxo-2-penten-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 24. A compound according to claim 1 which is p-bromophenacyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 25. A compound according to claim 1 which is phthalidyl 6-(3-cyano-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 26. A compound of the formula (V): ##STR118## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a pharmaceutically acceptable ester group; and X is an oxygen atom or CR.sub.6 R.sub.7 wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lower alkyl, or R.sub.7 is joined to R.sub.6 to form part of a carbocyclic ring of 5 to 7 carbon atoms.
- 27. A compound according to claim 26 wherein X is oxygen.
- 28. A compound according to claim 26 wherein X is a CR.sub.6 R.sub.7 group wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lower alkyl or is joined to R.sub.6 to form part of a 5 to 7 carbon atom carbocyclic ring.
- 29. A compound according to claim 28 wherein CR.sub.6 R.sub.7 is CHCOR.sub.9 or CHCO.sub.2 R.sub.9 wherein R.sub.9 is methyl, ethyl or benzyl.
- 30. A compound according to claim 28 wherein CR.sub.6 R.sub.7 is CHCN.
- 31. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (II): ##STR119## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a pharmaceutically acceptable ester group; A.sub.1 is hydrogen; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is hydrogen or hydroxyl; R.sub.3 is hydrogen or lower alkyl; and R.sub.4 is CHX wherein X is oxygen or CR.sub.6 R.sub.7 wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lowr alkyl or R.sub.7 is joined to R.sub.6 to form part of a carbocyclic ring of 5 to 7 carbon atoms or R.sub.4 is CH.dbd.CHCO.sub.2 R.sub.9, CH.dbd.CHCOR.sub.9 or CH.dbd.CHR.sub.10 wherein R.sub.9 is methyl, ethyl or benzyl and R.sub.10 is hydrogen, methyl, ethyl or benzyl, in combination with a pharmaceutically acceptable carrier.
- 32. A composition according to claim 31 wherein R.sub.4 is CHO, CH.dbd.CHCO.sub.2 R.sub.9, CH.dbd.CHCOR.sub.9 or CH.dbd.CHR.sub.10 wherein R.sub.9 is methyl, ethyl or benzyl and R.sub.10 is hydrogen, methyl, ethyl or benzyl.
- 33. A composition according to claim 31 wherein R.sub.3 is hydrogen or methyl.
- 34. A composition according to claim 31 wherein the compound has the cis-configuration about the .beta.-lactam ring.
- 35. A composition according to claim 31 wherein the compound has the trans-configuration about the .beta.-lactam ring.
- 36. A composition according to claim 31 wherein R.sub.1 is alkyl of up to 12 carbon atoms, alkenyl groups of up to 8 carbon atoms, phenyl or benzyl or said alkyl, alkenyl, phenyl or benzyl substituted by lower alkoxyl, lower acyloxyl, halogen or nitro.
- 37. A composition according to claim 31 wherein R.sub.1 is lower alkyl unsubstituted or substituted by lower alkoxyl.
- 38. A composition according to claim 31 wherein R.sub.1 is benzyl unsubstituted or substituted by lower alkoxyl, nitro or chlorine.
- 39. A composition according to claim 31 wherein R.sub.1 is a group of the sub-formula (a) or (b): ##STR120## wherein A.sub.3 is hydrogen or methyl; A.sub.4 is lower alkyl, lower alkoxyl, phenyl, phenoxyl, benzyl or benzyloxyl; A.sub.5 is hydrogen, methyl or methoxyl; and A.sub.6 is hydrogen, methyl or methoxyl or R.sub.1 is phthalidyl or phthalimidomethyl.
- 40. A composition according to claim 31 wherein R.sub.1 is benzyl.
- 41. A composition according to claim 31 wherein R.sub.1 is p-nitrobenzyl.
- 42. A composition according to claim 31 wherein R.sub.1 is phthalidyl.
- 43. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (V): ##STR121## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a pharmaceutically acceptable ester group; and X is an oxygen atom or CR.sub.6 R.sub.7 wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lower alkyl, or R.sub.7 is joined to R.sub.6 to form part of a carbocyclic ring of 5 to 7 carbon atoms, in combination with a pharmaceutically acceptable carrier.
- 44. A composition according to claim 43 wherein X is oxygen.
- 45. A composition according to claim 43 wherein X is a CR.sub.6 R.sub.7 group wherein R.sub.6 is hydrogen, lower alkyl, phenyl, CN, COR.sub.8 or CO.sub.2 R.sub.8 wherein R.sub.8 is lower alkyl, phenyl or benzyl and R.sub.7 is hydrogen or lower alkyl or R.sub.7 is joined to R.sub.6 to form part of a carbocyclic ring of 5 to 7 carbon atoms.
- 46. A composition according to claim 45 wherein CR.sub.6 R.sub.7 is CHCOR.sub.9 or CHCO.sub.2 R.sub.9 wherein R.sub.9 is methyl, ethyl or benzyl.
- 47. A composition according to claim 45 wherein CR.sub.6 R.sub.7 is CHCN.
- 48. A composition according to claim 31 wherein the compound is benzyl 6-(2-oxoethyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 49. A composition according to claim 31 wherein the compound is benzyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 50. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of 2,2,2-tricholoroethyl-6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclohept-2-ene-2-carboxylate, in combination with a pharmaceutically acceptable carrier.
- 51. A composition according to claim 31 wherein the compound is phthalidyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 52. A composition according to claim 31 wherein the compound is phthalimidomethyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 53. A composition according to claim 31 wherein the compound is phthalidyl 6-(2-oxoethyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 54. A composition according to claim 31 wherein the compound is phthalidyl 6-(4-oxo-2-penten-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 55. A composition according to claim 31 wherein the compound is pivaloyloxymethyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 56. A composition according to claim 31 wherein the compound is p-nitrobenzyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 57. A composition according to claim 31 wherein the compound is benzyl 6-(3-cyano-2-propen-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 58. A composition according to claim 31 wherein the compound is benzyl 6-(4-oxo-2-penten-1-yl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 59. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of p-bromophenacyl 6-(3-methoxycarbonyl-2-propen-1-yl)-7-oxo-1-azabicyclohept-2-ene-2-carboxylate, in combination with a pharmaceutically acceptable carrier.
- 60. A composition according to claim 31 wherein the compound is phthalidyl 6-(3-cyano-2-propen-1-yl(-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate.
- 61. A composition according to claim 31 in unit dosage form wherein each dosage unit contains 50-500 mg of said compound.
- 62. A composition according to claim 31 in parenteral administration form.
Priority Claims (1)
Number |
Date |
Country |
Kind |
11747/77 |
Mar 1977 |
GBX |
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CROSS REFERENCE
This is a continuation of Ser. No. 887,844, filed Mar. 17, 1978, now abandoned.
US Referenced Citations (4)
Foreign Referenced Citations (1)
Number |
Date |
Country |
56-7759 |
Jan 1981 |
JPX |
Continuations (1)
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Number |
Date |
Country |
Parent |
887844 |
Mar 1978 |
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